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United States Patent [191 [11] Patent Number: 4,863,636 Chang Et 21

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United States Patent [191 [11] Patent Number: 4,863,636 Chang Et 21 United States Patent [191 [11] Patent Number: 4,863,636 Chang et 21. [45] Date of Patent: Sep. 5, 1989 [54] SUBSTITUTED [56] References Cited N-HYDROXYPHTHALIMIDES AND THEIR U.S. PATENT DOCUMENTS USE AS DETERGENT ADDITIVES 3,767,671 10/1973 Klebe et a1. .... .. 548/473 [75] Inventors: Laurence W. Chang, Orange, Conn.; 3,915,879 10/1975 Barnett et al. ...................... .. 560/37 Robert G. Fischer, Stevensville, Primary Examiner-Paul Lieberman Canada Assistant Examiner-Christine A. Skane [73] Assignee: American Cyanamid Company, Attorney, Agent, or Firm-Steven H. Flynn Stamford, Conn. [51] ABSTRACT [21] Appl. No.: 156,131 N-hydroxyimide compounds derived from substituted phthalic anhydride are provided which exhibit strong [22] Filed: Feb. 12, 1988 metal ion chelating ability, making them useful as deter [51] Int. Cl.4 .................... .. C11D 3/28; C07D 209/48 gent additives, in boiler water systems, as reaction inter [52] US. Cl. .................................. .. 252/542; 252/544; mediates, etc. A detergent composition containing N 252/ 545; 252/546; 548/473; 548/475; 560/37; hydroxyimide and/or carboxy hydroxamic acid deter 562/450; 562/430 gent additives is also disclosed. [58] Field of Search ................ .. 548/473, 475; 560/ 37; 562/450, 430; 252/542, 544, 545', 546 9 Claims, No Drawings 4,863,636 1 2 These and other objects are achieved, according to SUBSTITUTED N-HYDROXYPHTHALHVIIDES the present invention, by compounds having the for AND THEIR USE AS DETERGENT ADDITIVES mula The present invention relates to chelating agents (I) which are useful as adjuvants for detergents and to detergent compositions, particularly fabric-washing detergent compositions. In particular it relates to novel N-hydroxyimide compounds having good transition metal ion chelating properties and to detergent compo sitions comprising at least one detersive surfactant and an effective amount of an N-hydroxyimide detergent additive. wherein R is carboxy, sulfo, or caroxyalkyl or sulfonal kyl having 1-12 carbon atoms, or alkali metal salts BACKGROUND OF THE INVENTION thereof; and X is hydroxy or ——O"M+, where M+ is an Detergent compositions have long employed materi alkali metal cation (i.e., Li+, Na+, K+, etc.). als, known as “builders”, to improve the detergency of Also contemplated are ring-opened derivatives of the soaps and synthetic detergents by actively chelating the Formula I compounds, which have the formula alkali metal cations which are normal components of “hard” tap water. Such builders have been found to (II) affect, for instance, soil suspension, emulsi?cation of II soil particles, solubilization of water-insolubles, and inactivation of various mineral constitutents present in a detergent system. Many materials useful as builders have been proposed, and their effects are known. See, ll e.g., US. Pat. Nos. 3,852,213, 3,950,260, 4,182,718, and OH 4,440,646 (all incorporated herein by reference). Recently, however, the attention of detergent manu wherein X and R are as de?ned above. facturers and researchers has turned.to the role of Also contemplated herein are detergent compositions heavier metal cations, i.e., transition metal cations, in comprising one or more detersive surfactants and one the formation of stain complexes on fabrics and other or more detergent additives consisting essentially of surfaces. It has been observed that these multivaleut N-hydroxyphthalimide compounds having the formula transition metal cations, particularly iron (Fe+++, en hance the binding of the components of many stains to 0 0 substrates, and breaking up the cation-enhanced bonds II II is an effective approach to stain removal. Therefore, X there is a strong need for the discovery of new materials R N-X or R that are effective as chelating agents for transition metal III-X cations, are easy to prepare, and can be added to deter as 1'. H gent compositions in economical amounts to boost stain-removing power. It has now been discovered that certain cyclic N where X and R are as defined above. hydroxyimide compounds derived from substituted DETAILED DESCRIPTION OF THE phthalic anhydride are active metal ion chelants and are 45 INVENTION useful as detergent additives. The N-hydroxyphthali mides of the present invention are water-soluble and The N-hydroxyimide detergent additives of the pres form soluble chelates with transition metal ions which ent invention are advantageously prepared by reacting a hinder detergent action and form stain complexes on substituted phthalic anhydride with hydroxylamine or a fabrics and other substrates. In basic solutions, e.g., 5 O salt thereof to obtain the N-hydroxyimides of the pres above about pH 9, ring-opened derivatives of the N ent invention. The substituted N-hydroxyimide com hydroxyphthalirnides are believed to be produced, pounds may be further reacted in the presence of base to yielding carboxy hydroxamic acid-functional deriva obtain ring-opened substituted mono-hydroxamated tives which are active metal ion chelants as well. phthalic acid. Thus, a typical reaction scheme for the 55 preparation of detergent additives according to the SUMMARY OF THE INVENTION present invention is as follows: It is therefore an object of the present invention to provide a new class of metal ion chelating agents. 0 It is a further object of the present invention to pro II vide new detergent additives which are active in stain 60 removal. ' R O substituted phthalic It is a further object of the present invention to pro anhydride vide a detergent additive free of phosphorus. It is a further object of the present invention to pro vide a novel detergent composition. 65 It is a further object of the present invention to pro H2NOH hydroxylamine vide a fabric-washing detergent composition that is effective in stain removal. 4,863,636 4 -continued compounds, and the variety of spacings possible (from 0 molecule to molecule) between the functional groups, II may enhance the metal chelating effectiveness of the compounds by allowing them to sequester a wider vari R N-OH substituted N-hydroxy ety of cations. phthalimide The N-hydroxyimide compounds and derivatives are active stain removers and are advantageously included in a detergent composition, in accordance with the present invention. A detergent composition of this in OH“ vention will contain at least one detersive surfactant. Such surfactants will be present in amounts usually encountered in detergent compositions, e. g., from about 0 ll 1 to about 50% by weight, preferably about 5 to about 25% by weight for fabric-washing detergents, and most OH 15 R substituted mono preferably from about 10 to about 20% by weight based N-OH hydroxamated phthalic on the total weight of the detergent composition. The H acid surfactants may be anionic, nonionic, cationic or am 0 H photeric, and mixtures of different detersive surfactants may be used. Non-limiting examples of suitable deter Phthalic anhydride is a well-known intermediate in sive surfactants include: the manufacture of, e. g., inks and synthetic resins. Many (a) Anionic surfactants: soaps, i.e., alkali metal (pref substituted phthalic anhydrides suitable for use in the erably sodium or potassium) salts of long-chain fatty present invention are also known. Carboxy-substituted acids containing from 8 to 20 carbon atoms, such as phthalic anhydride, e.g., 1,3-dioxo-5-phthalancarboxy lauric, myristic, oleic, palmitic, capric, caprylic, and lic acid (“trimellitic anhydride”), is a well-known inter stearic acids, used singly or in mixtures of differing mediate in the preparation of resins, adhesives, poly chain lengths; alkali metal salts of organic sulfuric reac mers, dyes and printing inks. The substituted phthalic tion products having long hydrocarbon chains of about anhydride compounds suitable for use in preparing the 8 to about 20 carbon atoms and a radical selected from N-hydroxyphthalimide compounds of the present in the group consisting of sulphonic acid and sulfuric acid vention will have terminal carboxylic acid or sulfonic ester radicals, such as sodium or potassium alkyl sul acid groups bonded directly or by a C1-C1; alkylene phates, preferably those obtained by sulphating higher bridging group to the benzene ring of the phthalic anhy dride moiety. Carboxy-substituted phthalic anhydride (C3-C3) alcohols; sodium or potassium alkyl benzene and sulfo-substituted phthalic anhydride are preferred. sulphonates in which the alkyl group contains from Reaction of the substituted phthalic anhydride to 35 about 9 to about 20 carbon atoms, such as sodium linear obtain N-hydroxyimide products may be accomplished alkyl (Clo-C15) secondary benzenesulphonate, 2-phe by contacting the substituted phthalic anhydride with at nyl-dodecanesulphonate, 2-phenyl-octadecanesulphon least an equimolar quantity of hydroxylamine or a salt ate and 3-phenyl-dodecanesulphonate; alkali metal thereof, preferably hydroxylamine hydrochloride. The (preferably sodium) ole?n sulphonates, i.e., the mixture reaction will normally be carried out in the presence of 40 of detersive surfactants obtained from sulphonation of about 2-5 moles per mole of hydroxylamine of a basic Cg-Cgz olefins, preferably straight-chain alpha-ole?ns; agent, preferably an organic base such as sodium meth sodium alkyl glyceryl ether sulphonates, including oxide, sodium ethoxide, sodium acetate, pyridine, trieth ethers of higher alcohols derived from tallow coconut ylamine, or quinoline. Most preferably, the reaction will oil and synthetic alcohols derived from petroleum; so be carried out in an alcoholic solvent, such as methanol 45 dium coconut oil fatty acid monoglyceride sulphates or ethanol. and sulphonates; sodium or potassium salts of sulfur The product may be isolated in any one of a number acid esters of the reaction between higher fatty alcohols of known ways. For example, the product can be iso (e.g., tallow or coconut oil alcohols) and ethylene ox lated by precipitation from a non-solvent, such as hex ide; the esteri?cation products of fatty acids with isethi ane, and the precipitate ?ltered, washed and dried onic acid, neutralized with sodium hydroxide; and so under vacuum to give the N-hydroxyimide product.
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